Sermon session

Two Sons

Session #129 Two Sons

Scripture Matthew 21:28-32

Summary In Matthew 21:28-32,  the Parable of the Two Sons is simple and straightforward. That said, it is also surprising and shocking. On one hand, it focuses on doing. Yet, on the other hand, it seems to be about believing. Which is it? What exactly was Jesus telling the religious leaders? What is He saying to us as sons and daughters of God?.


“But what do you think? A man had two sons, and he came to the first and said, ‘Son, go, work today in my vineyard.’ He answered and said, ‘I will not,’ but afterward he regretted it and went. Then he came to the second and said likewise. And he answered and said, ‘I go, sir,’ but he did not go. Which of the two did the will of his father?” They said to Him, “The first.” Jesus said to them, “Assuredly, I say to you that tax collectors and harlots enter the kingdom of God before you. For John came to you in the way of righteousness, and you did not believe him; but tax collectors and harlots believed him; and when you saw it, you did not afterward relent and believe him. Matthew 21:28-32

We have come to the section where Jesus shared three parables, one after another. Clearly, all three parables are related, making a collective point but each has its own emphasis. In the parable of the two sons (Matthew 21:28-32) , it is about the rejection of instruction. In the parable of the wicked vinedressers (Matthew 21:33-46), it is about the rejection of inspection. Finally, in the parable of the wedding feast (Matthew 22:1-14), it is about the rejection of invitation. These parables all warn against the consequence of rejecting God’s authority – Jesus’ authority. We will explore the parable of the two sons in this teaching, and then the other two in subsequent sessions.

If you are a parent, you will find the parable of the two sons very real and totally relatable. Most likely, you have experienced it more than a few times before in your own household. I know I have; not just as a parent, but also as a son. But Jesus was not teaching at a parenting seminar or a family conference. To understand and interpret the parable(s) correctly, we must consider the setting carefully.

Where was Jesus? Jesus was in the temple. He entered Jerusalem on Sunday; did the temple cleansing on Monday; and was back in the temple on Tuesday, teaching the kingdom of God. What was the setting? From Matthew 21:23-27, we understand that Jesus was engaged right in the middle of a confrontation with members of the Sanhedrin, the highest council (or authority) of Israel. What prompted the telling of the parable? The leaders had questioned Jesus’ authority. This provides the backdrop. When challenged by Jesus in return about John the Baptist’s ministry and authority, they ‘acted blur’ and refused to answer the question. Jesus provided the answer to His own question by way of this parable and two more later on.

What is the point of the parable? This is revealed in the question that Jesus asked in Matthew 21:31, “Which of the two did the will of his father?” They said to Him, “The first”. So we see it is about obedience. But it is also revealed in His own explanation in Matthew 21:31-32.  Jesus said to them, “Assuredly, I say to you that tax collectors and harlots enter the kingdom of God before you. For John came to you in the way of righteousness, and you did not believe him; but tax collectors and harlots believed him; and when you saw it, you did not afterward relent and believe him. Here, it is about believing. So is it about obedience or believing? The answer is YES. The parable of the two sons is very simple and straightforward. I believe Jesus intended it to be exactly that. That said, the point of the parable is also very surprising and extremely shocking.

Firstly, it is about authority. Against this context, we understand the place of believing and of obedience. Specifically, it is about obeying and carrying out the instructions of the One in authority; the Father’s will. That is why Jesus asked clearly and precisely, “Which of the two did the will of his father?” Lest one thinks it is all about works, the message of grace is clearly presented and emphasised. This offer by grace becomes even more pronounced when we realise that even in Jesus’ warning against those who reject His authority, grace is extended.

So, what is the parable of the two sons about? It is about authority, believing, obedience, the Father’s will and grace.

It is about AUTHORITY (and Submission to that Authority)

Let us remember the backdrop. The leaders had questioned Jesus’ authority in Matthew 21:23, “By what authority are You doing these things? And who gave You this authority?”. Jesus answered them by asking them about John’s authority. The leaders evaded the question. Jesus then established John’s authority, thereby affirming His own authority. Jesus did it indirectly, but precisely, through the parable of two sons- an easily identifiable and relatable story of father and sons. Clearly, the father represents God as the ultimate authority. The sons were expected to honour their father, to submit to the father’s authority and carry out his instructions. The first son said no; but later relented, and did as told. The second son said yes; but did not carry out that promise at all.

The punchline in this parable is when Jesus asked “Who did the will of his father?”. The leaders  answered promptly “The first son”;  as at this point, they have considered themselves as the first son. After all, they thought they were doing so much. Jesus then presented the twist that the first son was not them but the tax collectors and prostitutes; who recognised and acknowledged John’s authority. In other words, the leaders were more like the second son – the one who said ‘yes’ but did nothing about it. That was a big slap on their faces. Firstly, they were indicted for not believing John and so Jesus. Secondly, they were indicted for being disobedient to God. As leaders, they were expected to know the instruction of God; or would have said ‘yes’ to God’s will. However, they were hypocritical and fruitless. They were busy, full of activities but with nothing to show for it. This was a blatant rejection of instruction to do the Father’s will; disobedience at the highest level. Thirdly, they were told that they were not a part of the kingdom. Fourthly, even worse, others deemed less worthy make it to enter the kingdom of God before them or instead of them.

The parable is about authority. If you truly recognise and acknowledge God’s authority, you must submit to that authority by obeying and carrying out the instructions of that authority. By rejecting God’s instructions, you reject God’s authority. If you reject God’s authority by taking things into your own hands and living as if you are your own authority, you will finally be rejected by God. This becomes clearer, more intense and more urgent through the parables.

It is about BELIEVING

In explaining the point of the parable, Jesus mentioned believing a few times in Matthew 21:31-32, that the leaders did not believe John but the tax collectors and harlots did and if they had observed that they should have relented and later believed.

The parable is about doing. But Jesus’ point was about believing. It is too easy to presume and preach that Old Testament salvation is about doing; and that New Testament salvation is about believing. This would be ignoring the entire context of Matthew 21 which is about hypocrisy and fruitlessness. Jesus’ answer about believing extended from Matthew 21:25. It is about leaders not believing John’s ministry and acknowledging his authority from heaven. 

To believe in John’s authority is to repent, to turn and to return, to live rightly, to bear fruit worthy of such repentance. However, the leaders did not believe they needed to repent. They considered themselves righteous by the law. They missed the point that they were proud, self-righteous, hypocritical and legalistic. 

To believe in John’s authority also means to believe in Jesus’ authority because John pointed to Jesus.

By affirming Jesus’ authority, it also confirms all that Jesus said and did in Matthew 21 – temple cleansing and fig tree cursing. Both of these pointed to hypocrisy and fruitlessness. This refers to a lack of doing on the leaders’ part as well as useless unproductive doing with no result. The connection between believing and doing is very clear. Yes, it is about believing. But right believing will always result in right doing. This is totally consistent with the rest of Scriptures. In Luke 6:46, Jesus said “But why do you call Me ‘Lord, Lord,’ and not do the things which I say?” i.e., if you want to acknowledge My authority, if you believe Me and call Me Lord, then you must be obeying and doing the things which I say because I hold the authority and I expect you to submit to that. In James 2:20, the apostle James said, “ But do you want to know, O foolish man, that faith without works is dead?” i.e., if you say you believe, something must come out of that belief. Believing must lead to doing. But did not John say “just believe”? In John 3:16, he wrote “whoever believes shall not perish but have eternal life”. Indeed he said that but John also said, “but he who does the will of God abides forever.” (1 John 2:17). So it is believing and doing.

It is about OBEDIENCE

Obedience is doing out of right believing. In this parable, we see two kinds of obedience: delayed obedience and declared obedience. The first son displayed delayed obedience. He outrightly rejected the instruction first and disobeyed. So before delayed obedience is disobedience. Later, he regretted (changed his mind) and obeyed. Delayed obedience is still obedience as he did what he was asked to do, albeit later.

The second son displayed declared obedience, saying ‘yes’ and not following through with it and it  is plainly disobedience. It does not matter how impressively you declare obedience. As long as nothing is done, it is still disobedience. 

Which son am I? Delayed Obedience or Declared Obedience? At times, I am like the first son, delaying obedience. I wish I am able to respond with immediate obedience all the time. Truth is, as far as I can remember, most of my obedience is delayed obedience. Before that, I am either rejecting why I should do it or rationalising why I am not able to do it. By the time I finally obey, it is usually delayed. At other times, I am like the second son displaying declared obedience. In my enthusiasm, and good intentions, I respond positively with a yes and an amen; but I find it hard to follow through. I mean really well, I assure you, but for some reasons, I just do not follow through. I do not even realise it. In fact, I am quite impressed with myself, for being so ‘obedient’ all the time.

Which son are you more like? Declared obedience is potentially deceptive – talk is cheap. Delayed obedience is still obedience

It is about the FATHER’S WILL

Obedience is doing as instructed by God. But exactly, obedience to what? Jesus taught us to pray  in Matthew 6:10, “Your kingdom come. Your will be done; on earth as it is in heaven”. It is obedience to God’s Will, or the Father’s Will ; not my own will. This can refer to the general will which leads to general obedience as well as specific will which leads to specific obedience.

General obedience is when we walk according to His laws, His will and ways, in righteousness and with love; as opposed to “lawlessness”. As we walk according to the ways of the kingdom, we guard against lawlessness. Jesus warned those who had prophesied in His name, cast out demons, i.e., those who had done a lot of ministries, churchy type activities but did not walk the way of the kingdom, they had failed in general obedience.  (Matthew 7:21-23). 

The more we align to kingdom living and obey generally that general will, it helps us to posture our heart for the specific things that the Lord wants us to do, the specific obedience. Specific obedience refers to what God’s will is for each of us and refers to our specific kingdom assignments. An example is Jesus’ specific assignment at the cross in Matthew 26:42. No one else can do this on His behalf. Similarly, there are specific assignments that no one else can do on our behalf. 

So general and specific obedience are expected of all children of God. Those who believe in Jesus become children of God (John 1:12) but according to Jesus, the true family of God are those who obey and do the Father’s will – sons and daughters who serve the Father’s business, who do the Father’s will. (Matthew 12:50). It is not just about believing but about obedience to the Father’s will, not just obedience to attend church and go to a cell group which is a good start. The more we align to the heart of the Father, the more we discover the will of God and therein also discover our own specific kingdom assignment. It is about the Father’s will.

It is about GRACE

Jesus referred to the tax collectors and the harlots entering the kingdom of God even before the religious leaders. This is extremely shocking and surprising, if not totally offensive. The leaders would have thought how these people even deserve to come into the kingdom of God and that they themselves were excluded.

Entering the kingdom is by grace through faith. It cannot be about works i.e. salvation by works is just not possible (Ephesians 2:8-9). We become sons and daughters of God by grace. However, once we become sons and daughters of God, we are expected to submit to His authority, to obey and fulfil the Father’s will, as evidence and genuineness of our faith (Ephesians 2:10). The same grace that enables entry into the kingdom enables effectiveness in the kingdom (1 Corinthians 15:10).

Embedded in this parable is grace to both sons, to both groups whether it was delayed obedience or declared obedience. The space between disobedience and delayed obedience is grace. He is gracious and He allowed the chance upon chance upon chance for obedience finally.  The space between declared obedience and demonstrated obedience is grace. God is gracious to wait for us to obey. Grace is still available for all of us to relent, to regret, to repent, to change, to come to our senses, to obey, to submit to the instructions to the authority that we declare we are submitted to. We thank God that while we are in the space between disobedience and obedience that there is grace waiting for us. 

Leaders were compared to those they thought were unrighteous, unholy and unworthy. Tax collectors and prostitutes (a Matthean phrase that included the worst of the worst) – sinners enter the kingdom of God by grace. Instead of seeing the grace that was similarly extended to them, the leaders became upset with grace extended to others. Though the time was short, the leaders still had a chance to change their ways. This is seen in the last phrase (Matthew 21:32),  “and when you saw it, you did not afterward relent and believe him.” Jesus was announcing grace and extending grace to the leaders. Sadly, instead of heeding, they hardened their hearts even more. In rejecting the authority of Jesus, they rejected the grace that comes with that authority.

It is about grace. Do not miss the grace in this parable and Jesus continues to extend that grace because it is about grace.


The parable of the two sons is simple and straightforward. It is about authority. Against this context, we then understand the place of believing and of obedience. More specifically, it is about obeying and carrying out the instructions of the One in that authority; the Father’s will. Lest one thinks it is all about works, the message of grace is also clearly presented and emphasised through the parable.

The parable of the two sons is also surprising and shocking. In first century Israel, no Jew would ever have accepted the charge that he was not working for God,  much less the religious leaders to whom this parable was directed. However, that is precisely Jesus’ point and the shock value of this parable. We must be careful not to be presumptuous and be caught off-guard like the religious leaders.

Using each of the three characters of the parable, Craig Blomberg (The New American Commentary: Matthew)  sums up the three key points of the parable as follows:

Like the father sending his sons to work, God commands all people to carry out his will.
Like the son who ultimately disobeyed, some promise but do not perform rightly and so are rejected by God.
Like the son who ultimately obeyed, some rebel but later submit and so are accepted.”
He goes on to present an even tougher truth, “ in the kingdom, performance takes priority over promise.”

Once more, in case you missed it: it is about authority, believing, obedience, the Father’s will, grace.

We close with one final point- It is about time:
If you have not yet acknowledged the authority of Jesus, it is about time you did. One day, everyone will have to account to this authority, to Jesus, the King of kings, the Lord of lords. No one can say they do not know or give any excuse.

If you have not yet believed in Jesus, it is about time you did. Believe in Jesus as the only one who can save you into His glorious kingdom.

If you have not yet obeyed Jesus, it is about time you did. Whether declared or delayed obedience, obedience is never too late until it is too late. Do not wait any longer. Now is the time to obey.

If you have not yet discovered or done the Father’s will, it is about time you did. Start with general obedience. Walk in His ways and His will. The more you align with the Father’s heart, the clearer you will be about the Father’s business. Be ready for specific obedience. Be faithful to fulfil your kingdom assignments.

Lastly, if you have not yet responded to the grace that is extended to you, it is about time you did. This “space of grace” does not remain available forever. Whether to enter into the kingdom or to be effective for the kingdom, it is entirely by His grace, His grace, His grace. Do not presume upon this privilege. Do not receive this grace in vain. Instead, be sustained and empowered by His grace.